3-(3-Cyano-4-(isopropylsulfonyl)phenyl)-1,1-dimethylurea → 3-(3-(Aminomethyl)-4-(isopropylsulfonyl)phenyl)-1,1-dimethylurea

HRID 1667614Notes

Reaction equation

HRID 1667614 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])[CH:6]=[CH:7][C:8]=1[S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10])#[N:2]>C1COCC1.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:20])[N:17]([CH3:18])[CH3:19])[CH:6]=[CH:7][C:8]=1[S:9]([CH:12]([CH3:14])[CH3:13])(=[O:11])=[O:10]

Participants

4

Reactant 1

HCID 574482113-(3-Cyano-4-(isopropylsulfonyl)phenyl)-1,1-dimethylurea

Product 1

HCID 574482123-(3-(Aminomethyl)-4-(isopropylsulfonyl)phenyl)-1,1-dimethylureaYield 91.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 16A (45 mg, 0.15 mmol) in THF (10 mL) was added Raney Ni (cat.) and the mixture was hydrogenated at 60 psi for 4 h. The reaction was filtered and concentrated to provide 16B (41 mg, 91%). LC-MS: 300.37 (M+H)+

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1dad46d135e0485fbe1d2dbc9d070ddf
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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